Letters to my sons

A collection of thoughts and lessons I've learned along the way for my little men,
and anyone else that's interested.

My sons,

I have had the unnatural privilege of working closely with several great orators of my time. Powerhouse communicators who could not only take complex concepts and ideas and distill them down to their essence but inspire you to run hard after them. Leaders who could not only move organizations but could shape the industry simply by speaking. Being in the presence of leaders like Anders Hjelsberg, Elissa Murphy, and Blake Irving has given me the distinct experience not only of being inspired by the best, but of being able to witness the life changing power of great communication.

We’ve discussed the need to understand yourself first and foremost as a primary participant in communication. We’ll now move on to the second party in any communication: your audience.

Early on in my career I was lucky enough to be on a team that allowed me the opportunity to speak and present to our customers. As a part of the deal, I got to spend a bit of time with a speaking coach that helped me refine my presentation skills, and something she said to me very early on has stuck with me. She informed me that whenever you are communicating anything,

your audience will have a predetermined set of thoughts, questions, concerns, and worries that will prevent them from truly hearing you until addressed.

Whether we’re talking about a presentation to my execs, trying to convince my partner of a particular vacation spot, or advocating for my children to try something new, each of them will have a set of concerns that need to be addressed before they can hear me. So how do I figure out what those are, and by doing so address them and give myself the best chance of being truly heard?

The art of seeing people

I’ve been on a journey to build better relationships. With my children, with my partner, with my aging parents, with my brother and his wonderful family, with close friends, and with my team, I’ve been on a mission to figure out how to build deeper and stronger connections across the gamut of these relationships. I read a wonderful book last fall by David Brooks called How to know a person that discussed in depth not only how to know people well, but various character traits that prevent us from knowing others and from achieving that level of vulnerability and trust that breathe life into relationships.

So before we get into how to see people and understand them, I thought it would be fun to take a quick antagonist view at how not to see people well, and for us to honestly evaluate how many of these traps we fall into. So without further ado, the list!

  1. Egotism. This is the trait that makes us simply not interested in other people. We are self-absorbed, self-interested, dare I say self-obsessed. Instagram culture (or TikTok or whatever the latest craze of the day happens to be) further exacerbates this problem, but make no mistake: this is a huge problem with our world!
  2. Anxiety. Have you ever taken time to listen to what’s going on inside your head? There are many studies that show that there is so much noise going on in our own heads that we are unable to even think about other people with all that racket going on! There’s a really great book I read recently called The Anxious Generation that talks about the increase in anxiety if you’re curious to learn more.
  3. Naive realism. This is the quality that believes that our own point of view is the objective truth. Youthful zeal often falls into this trap, but the reality is that we all interpret the world with our filters; we do not see the world as it is.
  4. Lesser minds problem. This is a funny one. This is simply the act of thinking everyone else is dumber than we are. Sadly, this happens much more often than we’d like to admit.
  5. Objectivism. Instead of seeing others as people, we see them in the groups that they belong to and detach emotion from the situation altogether. We do this at work a lot - instead of saying “so and so’s team is failing”, we say “team x is failing”, removing the human element from the interaction.
  6. Essentialism. This is effectively stereotyping, boiling people down to their essential common traits instead of seeing them as complex beings with much depth and unique experience.
  7. Static mindset. Also known as a fixed mindset, this is the belief that people don’t change. Once we’ve made up our minds about someone, we hold onto that frame and do not give any consideration to the changes that they undergo.

Ever fall into any of those traps? I certainly have, and it has undoubtedly prevented me from understanding others, from developing better bonds, and from being more effective in my communication with them.

The good news is that these are not insurmountable. With a little bit of awareness and a lot of hard work, we can indeed change these traits and begin to see people as they are, not as we imagine them to be, and in doing so understand how to better communicate with them.

So how do we learn to see people, to understand what makes them tick, and to figure out how to be most effective in our relationships and communications with them?

1. Be aware of your attention

We live in an attention economy. Companies and products no longer vie for our money as a primary; no, they vie for our attention. Attention is money. Monthly active users. Daily active users. Hours spent per session. All of these are metrics that any company worth their salt tracks and tries to maximize.

It is that technological and social environment that we find ourselves in, and it therefore behooves us to understand why our attention matters, and what forces we fight against when we try to control that attention.

First of all, know that there are two types of attention: spotlight and starlight. Spotlight attention is our ability to focus actively on a single task or conversation intently and intentionally, whereas starlight attention is our ability to have a longer term sustained focus on goals and objectives.

In order to really see a person, we must be able to start by applying our spotlight focus to them in our interactions, which in turn allows us to eventually apply our starlight focus. We’ve got to take a few intentional steps:

  1. Be present. This is becoming so hard for people that every training or offsite I’ve attended in the last 5 years has started with a strong reminder to be present.
  2. Remove distractions. In other words, don’t take out your phone. Not only does it not allow you to focus your spotlight attention on someone, it also makes them feel less important and not seen.
  3. Treat attention as all or nothing. Sit up, lean forward/lean in, ask questions, and show positive signs of understanding. This may mean nodding when appropriate, or adding +1s or whatever is culturally accepted for you to do.

Our attention matters. A lot. It conveys respect, care, and consideration. It tells the other person we want to know them.

2. Be an active listener

Most of us believe that we’re decent listeners - 96% of us according to a recent HBR study, but 34% of adults in America feel misunderstood “often” or “very often”. What gives?

First, we need to understand that there are different levels of listening:

  1. Self-focused listening. This is where the listener is really thinking about how they will respond more than they are listening.
  2. Person-focused listening. This is where the listener is solely focused on what the speaker is saying.
  3. Environment-aware listening. This is where the listener is not only focused on what the speaker is saying but on what the context, environment, other people in the room etc are doing as well.

That same HBR study showed that the vast majority of us are self-focused when we listen. We are thinking about how to respond. We need to graduate beyond that! The more we are able to actively engage in listening, the more we are able to draw the other party/parties of our communication into an active partnership of give and take, of dialogue, and of common understanding.

Knowing your audience

Regardless of whether we’re chatting 1-1 with someone, hanging out in a group of friends, in a meeting at work, or speaking in front of thousands, it is on us as the speaker to understand the receiver so that we frame our words in a way that the other person can hear.

A face to face interaction requires focused attention with good back and forth. The more we actively listen to them, the more they will feel heard and will be willing to connect and further the conversation.

A group conversation requires environment awareness and perceptiveness as to each person’s state. The more we understand each member of the group’s feelings, inclinations, and worries, the more we can ensure they are engaged.

A large presentation requires understanding where your audience is coming from, what their cares and concerns are. The more we do our research and learn about the cares and perspectives of those sitting in the audience, the more relatable we can be to them.

The most effective communicators are able to understand their audience, are in tune with their cares and worries, and are able to adjust not only what they say, but how they say it to give their listeners the greatest chance of hearing deeply what the speaker is trying to communicate.

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